Stay Cool

Stay Cool (Shoulda. Coulda. Woulda.)

A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.

Where to Watch

US▼

Amazon Prime Video

fuboTV

Amazon Prime Video with Ads

Shout! Factory Amazon Channel

The Roku Channel

Fandango at Home Free

Pluto TV

Amazon Prime Video Free with Ads

Tubi TV

Google Play Movies

YouTube

Fandango At Home

View on JustWatch →

Top Cast

Winona Ryder

As Scarlet Smith

Mark Polish

As Henry McCarthy

Sean Astin

As Big Girl

Hilary Duff

As Shasta O'Neil

Josh Holloway

As Wino

Jon Cryer

As Javier

Chevy Chase

As Principal Marshall

Jessica St. Clair

As Darcy Portola

Frances Conroy

As Mrs. Leuchtenberger

Marc Blucas

As Brad Nelson

More Like This

Beauty & the Briefcase

2010

Gia

1998

Fired Up!

2009

Catch That Kid

2004

She Wants Me

2012

The Last Dolphin King

2022

Margin Call

2011

Titanic

1997